Silicon‐Modified Carbohydrate Surfactants III: Cationic and Anionic Compounds

Wagner, R.; Richter, L.; Weiland, B.; Weißmüller, J.; Reiners, J.; Krämer, W.

doi:10.1002/(sici)1099-0739(199706)11:6<523::aid-aoc617>3.3.co;2-p

Cited by 12 publications

(15 citation statements)

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“…The amidation of amine functional siloxanes has been reported previously by Wagner and colleagues (36)(37)(38)(39)(40)(41)(42). Equation 2 describes an easy one-step synthesis of the oligoethylene glycol diglycidyl ethers from oligoethylene glycols and epichlorohydrin under phase-transfer conditions (PTC) in the presence of sodium hydroxide.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Zhang

2004

J Surfact & Detergents

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A new family of glucosamide-based trisiloxane gemini surfactants of the general formula (CH 2 OCH 2 ) n (Me 3 SiOSiMeR 1 OSiMe 3 ) 2 (where R 1 = (CH 2 ) 3 NR 2 (CH 2 ) 2 NHCO (CHOH) 4 CH 2 OH; R 2 = CH 2 CH(OH)CH 2 OCH 2 ; and n = 0, 1, or 2) was prepared and characterized, both structurally and as aqueous surfactants. The monomer was prepared by amidation of the precursor amine functional trisiloxane with D-gluconic acid δ-lactone. Gemini surfactants were then prepared by the alkylation of the precursor secondary amine with oligoethylene glycol diglycidyl ethers. They were structurally characterized by proton and 13 C nuclear magnetic resonance and elemental analysis. Members of this family reduced the surface tension of water to approximately 21 mN/m at concentration levels of 10 −5 mol/L. These gemini compounds showed two critical aggregation concentration values. This behavior resulted from the formation of premicellar aggregates before true micelles were formed.In recent years, silicone surfactants have attracted considerable interest because of their many technical applications. Owing to their unique molecular structure compared with that of normal hydrocarbon surfactants, they have excellent surface-active properties for special purposes. They can also reduce the surface tension of water to lower values than can be obtained using traditional organic surfactants. Furthermore, because of their bulkiness and molecular structure, the adhesion forces between the individual molecules in interfacial films are small; for this reason, the compounds act as good wetting agents. Silicone surfactants are also known for their low physiological risk in cosmetic applications.In contrast, sugar-based surfactants have been known for many years. In recent years, they have begun to be produced on an industrial scale and their use has gradually increased because of their valuable properties, such as good dermatological compatibility, excellent biodegradability, and the absence of toxic effects.Over a decade ago, gemini (dimeric) surfactants, a new class of surfactants consisting of two hydrophobic chains and two hydrophilic headgroups connected by a relatively short (rigid or flexible) spacer, were developed. These dimeric compounds show improved surfactant properties compared with monomeric surfactants. Gemini surfactants have attracted considerable interest, since these compounds have much smaller critical micelle concentration (CMC) values, much greater efficiency in reducing surface tension than expected, and better aggregation behavior. Gemini surfactants have been generating increasing interest owing to their tunable molecular geometry and their superior performance in applications (the CMC of the gemini is very low, so less gemini may be needed to reduce the surface tension of the solution).The unique surfactant properties of gemini surfactants have prompted investigations by a number of researchers. Those that have been studied in greatest depth, in terms of their physicochemical behavior, have been the cationic gemin...

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Zhang

2004

J Surfact & Detergents

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“…In a separate conical flask 80 g of glucose was dissolved in 100 ml of isopropanol and heated to 60°C, then was added to the aminopropylpolysiloxane solution slowly, 10 ml every 5 min, after 60 min of addition the solution became homogenous. The reaction was monitored using Perkin Elmer FT-IR by observing the disappearance of the two stretching peaks of the amin group at 3400 cm À1 and the presence of a new peak at 3550 cm À1 and one peak for NAH at 3400 cm À1 [2]. The reaction held 2 h refluxing under nitrogen purging, the solution color will change from colorless to yellow color.…”

Section: Synthesis Of Glucose Grafted Polysiloxanes (Gps)mentioning

confidence: 99%

Synthesis and evaluation of some derivatives of polysiloxanes

El-Sukkary

Ismail

Rayes

et al. 2014

Egyptian Journal of Petroleum

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Silicone surfactants have been widely used in our daily life and many industrial fields on the basis of their unusual properties. Only in the past decades has the use of silicone as a hydrophobic building block for the preparation of surfactants become common. The recent trend to combine silicone, polyoxyalkylene and carbohydrate moieties in the same molecule has resulted in a plethora of new compounds with new properties.In this article, we report the preparation of a series of ''glycopolysiloxanes'' surfactants with different molecular weights. They were structurally characterized by IR, 1 H NMR and MS.Specifically, the critical micelle concentration (cmc), effectiveness of surface tension reduction (p cmc ), maximum surface excess (C max ), minimum surface area (A min ) and standard free energies of micellization (DG°m ic ) and adsorption (DG°a ds ) have been determined from aqueous surface tension measurements using Du-Nouy Tensiometer (KRUSS K6 type 4851) with a platinum ring. All the surfactants have good surface properties and have low cmc.The bacteriostatic power of these polymers was tested and compared under the same conditions in aqueous solution against common strains of Gram positive bacteria and strains of Gram negative bacteria.ª 2014 Production and hosting by Elsevier B.V. on behalf of Egyptian Petroleum Research Institute.

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“…And they were very good emulsifiers. Wagner et al [30] further reported quaternization of tertiary amino functions containing aminoalkylamides yields polyhydroxylated ammonium salts (Scheme 9).…”

Section: Prepared By Reacting the Aminosilicone With Glucosementioning

confidence: 99%